Things to Do in January in Chicago (2020)

This post covers the best things to do in Chicago this January, including, free, family-friendly, as well as nighttime activities, all updated for 2020.

 

 


TOP 10 EVENTS AND THINGS TO DO IN CHICAGO IN JANUARY

January in Chicago is a great time to experience because it is a slow season for tourism which means you won’t have to wait in lines or stand in crowds! 

For some of the more popular things to do in Chicago, read the following posts:


1) Go to a Sporting Event

There is nothing more Chicago than cheering on our sports teams! 

In January, you can head west to the United Center for a basketball or hockey game. 

 

 

For a list of all sporting events happening this month, check this list.

Hockey 

Basketball

Click here to find all sporting events happening this month.


2) Go to a Concert

January is the perfect month to stay inside and enjoy a concert during the cold evenings.

 

 

Here are just a few of the larger-scale concerts happening in January of 2020. 

For a list of all concerts happening this month, check here.

You can find all the concerts happening this month here.


3) Go on a Sightseeing Tour

Put on your parka and be sure to layer for our January tours!  Join our history-loving Chicago-adoring tour guides on foot.

We offer pay-what-you-like walking tours every day of the week in the Windy City. 

 

 

Try the Chicago Pedway tour to experience the indoor paths that run under the city or the Winter Loop Tour for a winterized Loop experience.

If you’d prefer to enjoy a bus tour, we have a great comparison of Chicago’s best. From hop-on-hop-off buses to dedicated tours, you’ll find one to suit you here.


4) Go to the Theater

Chicago is home to many many regional theatres, small black box spaces, and Broadway Tour houses. There is something for everyone!  

To see all the theatre productions happening this month, look here.

 

 

Here are just a few of the many shows happening in January 2020.

  • Blue Man Group runs continuously and is a great show for everyone in the family. They are famous for their funny mimed skits that incorporate dance, music, and electronic visuals.  
  • Hamilton at the CIBC Theatre runs until January 5, 2020. This is the story of Alexander Hamilton- performed with music and rap! 
  • Phantom of the Opera, a theatre classic, runs December 2019 – January 5, 2020.
  • Mean Girls is a fun, new musical adaptation of the movie that runs from December 25, 2019, to January 26, 2019.
  • Once on This Island that runs from January 21, 2020, to February 2, 2020, will help you imagine feeling warmer during the cold winter!

Check here to see a full calendar of all shows and get a real taste of Chicago theatre.

Pro-tip: Check out our self-guided theatre tour to admire the exterior of some of the oldest movie palaces in the downtown Loop.


5) See More for Less with a Chicago City Pass

Many of Chicago’s biggest attractions have entry fees. 

While you do pay for a tourist discount pass, it can give you a bulk discount and free admission into some interesting tours and museums, saving you up to 55%.

They can also save you time with skip-the-ticket-line privileges.

 

 

Each Chicago tourist discount pass includes a variety of fun activities and attractions.

Here are a few examples of what you can visit with a tourist pass, for a discount or for free.

For more details, make sure to read our full post covering Chicago tourist passes.


6) Sketch Comedy Festival

Perfect for the Comedy Capital of the world, this festive highlights over 1,000 performers in the 180+ shows that take place during these 10 days.

 

 

Founded in 2002 with just 35 local performers, Sketch Comedy Fest has now become the largest of its kind in the world, drawing in writers and performers from across the globe.


7) Ice Skating in Downtown Chicago

Ice Skating is a great way to spend the day or evening hours, especially with numerous rinks around the city.

There is the McCormick Tribune Ice Rink in Millennium Park.

Right underneath Cloud Gate and on the edge of the downtown area makes this a perfect spot, and you can warm up with some hot chocolate served right next to the rink. 

 

 

Across the bridge in Maggie Daley Park, you will find the Skating Ribbon

Surrounding the rock wall and with the skyline in the background, this is experience aims to give you the feeling of skating through the alpines. 

For both rinks, skating is free and rentals are $12 on weekdays, $14 on weekends.


8) Take a Tour of a Local Brewery

Are you in Chicago and looking where to find a good local pint? Chicago is a great city to enjoy a local microbrew in one of our fantastic neighborhoods.

Many restaurants have enough space to brew their own beer like Berghoff’s, Gino’s East, and Rock Bottom, but if you want to try multiple Chicago Brews, these bars are great.  

 

 

Everyone has their favorite places for a pint, of course.

Click here for Chicago Brewery Tours!


9) Indulge in Chicago Food

Explore Chicago’s delicious food! Head to a popular Chicago restaurant like Girl and the Goat to try Chef Stephanie Izzard’s amazing dishes. 

 

 

Another option is to head to one of our cities famous deep-dish places. Or head to Au Cheval for an amazing hamburger. 

Looking for a sweet treat? Try Stan’s Donuts with locally roasted coffee!  

If you are looking for something more casual – try a Chicago Hot dog or an Italian Beef sandwich!


10) Tomorrow Never Knows Music Festival 

For a decade, people have been braving the January weather for this music festival.

 

 

Tomorrow Never Knows celebrates up-and-coming local indie artists, as well as draws in national acts, musicians and comedians alike.

Hosted in different independent venues across this city, this provides a true Chicago experience.

The festival runs from January 15 – 19, 2020.

 


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THINGS TO DO AT NIGHT IN JANUARY

Chicago offers many free activities throughout the year. Here are a few suggestions during January 2020.

 

 

Be sure to read our post about the top things to do in Chicago at night for even more suggestions.


Adler After Dark

On the third Thursday of each month, Adler Planetarium opens up for a fun night-time event for adults. 

There will be drinks, music, and entertainment while enjoying looking at the stars. Escape the cold and enjoy this monthly event.


Check out a Drag Show

Head to the South Loop to attend Lips Drag show which has been around for 25 years. 

It has performances Wednesday – Sunday; including a Sunday brunch! 


MSI After Dark

The MSI After Hours is an Adults Only experience to explore the museum after the day time guests have left.

Each After Hours event lets you enjoy cocktails, beer, snacks, and new programs each month.


See the Local Music Scene

Check out the local music scene in Chicago, take a look at some of the more popular venues: 


Go Out for a Cocktail

Chicago has more speakeasies – fitting for the mobster history of the Windy City.

If you’re looking for more than just atmosphere and want to find one of the best Craft Beers, we can make sure you find a local pint.


Go to a Game Bar

Explore some of Chicago’s best game bars. Whether you want to try an arcade bar with some pinball and Packman or try a classic board game, Chicago has a bar for you. 

Check out our favorite game bars across the city

Be sure to check out our post on top things to do in Chicago at night for even more suggestions.

 


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FREE THINGS TO DO IN JANUARY

This section lists more free events, activities, and attractions so see in Chicago this month.

 

 

For more ideas, check out our post about the Top Free Things to Do in Chicago.


Maxwell Street Market

Bundle up to enjoy the international flare at this market on Sunday mornings between 7:00 am – 3:00 pm which has been a Chicago tradition for over 100 years.

Take in the bargains and culture at this year-round market.

The market has free admission. For more details, click here.


Take yourself out on a Self-Guided Food Tour

If you want to experience Chicago through your taste buds, try one of our self-guided food tours.  Head to Chinatown to explore and enjoy savory buns and Peking duck. 

Pilsen is a wonderful neighborhood where you can appreciate the rich Mexican culture of the area while enjoying tasty dishes. 

Small but might Little Italy is definitely a neat neighborhood to experience too! Get out of downtown to the northside neighborhood Andersonville for a little shopping and tasty bites in the Swedish neighborhood.


The Watertower Museum

Go into the bottom of the Watertower for a small but mighty free art museum! 

If you are joining us on our Pay-What-You-Like Magnificent Mile walking tour– you will enter this museum with your tour guide.


Art on the Mart

Most nights in January Art on the Mart will be in full swing! 

Head the Riverwalk at sunset to see an amazing art projection on the Merchandise Mart Building – a building so large, it has its own zip code! 


The Bridgeport Art Center

Located in the Bridgeport building which is a creative home for local artists and designers, there is an outdoor sculpture garden and three curated art galleries. 

On the 3rd Friday of each month between 7:00 pm – 10:00 pm, people are invited to see the painters, sculptors, photographers work.


Check out the Chicago Cultural Center

A great place to warm up while appreciating architecture is the Cultural Center. This beautiful and historic building is free and open for the public to explore.

Beyond the art that lines the walls, you will find free traveling films, lectures, and performances here. 

This is also a great place for children’s programming.

Check out their calendar of events to see what is going on during your visit.


Free Museums

There are many Chicago museums that are free! Check out our free museum list here.  

Also, if you happen to be a local traveler – be sure to check for free museum days during the winter months in Chicago.

For even more free activities, see our post on the top free things to do in Chicago.

 


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FAMILY-FRIENDLY THINGS TO DO IN JANUARY

Below we list several great options to keep your children entertained this month, including parks, museums, and theater!

 

 

Be sure to check out our post about family-friendly activities in Chicago for a more complete guide.


Winter WonderFest (November 30-January 6)

Navy Pier’s Festival Hall transforms into an indoor holiday theme park called Winter WonderFest, with music, skating, carnival rides, and entertainment.

Children shorter than 3 feet tall are free.

This is a great event for families with little kiddos and runs through January 6!


Northerly Island Adventure 

Head to Northerly Island to explore with the kids during some official free exploring days.

See birds of prey and wolves, make nature-inspired winter crafts, walk on snowshoes and drink cocoa at Polar Adventure Days on January 26, 2020

This event is free to attend.


See Corduroy the Play

See the play Corduroy, which runs November 15 – January 5, 2020, at the Broadway Playhouse performed by the Emerald City Theatre company. 

This is an excellent story for the whole family adapted from the children’s books about a.


Light Show in the Garden 

Head a stretch North to the Chicago Botanic Garden to see the new event Lightscape. The garden is transformed into a twinkly wonderland.

You walk on a one-mile path that includes majestic trees, water features, and stand-alone lighting installments.

The light show is active from November 22, 2019 – January 5, 2020.  


See Trolls Live at the Chicago Theatre

Sit in the iconic Chicago Theatre with the kids and watch Trolls Live! There are three performances per day. 

  • Dates: January 11 – 12, 2020
  • Times: 10:30 am, 2:00 pm, 5:30 pm
  • Prices: From $53+

Find tickets for Trolls Live! here.


Juice Box Concerts at the Cultural Center

Head to the Cultural Center with your family of little ones every first and third Friday and Saturdays at 11:00 am – 11:45 am for an engaging musical event!  

While this will be enjoyable for the whole family, it is geared to kids between the ages of 1-6.


Go to a Museum

January is a great month to have a few indoor options for the family in  Chicago so bringing the youngsters to an indoor museum is always a good idea!

Chicago has a lot of museums that are very interactive and ideal for kids such as:

 


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About the author

Manager | Chicago & Los Angeles

Mel loves to be a tourist in her own city. With a background in performing arts, tourism, and photography, giving tours and being a story-teller comes naturally to her. She loves traveling, food, and theatre. Mel splits her time between Chicago and Los Angeles (#theatrelife) and leads tours and manages both cities!